Not Your Average Death Blog
Just Because You Love Someone Doesn't Mean They're the Right Person for the Job
When I was first practicing law in Nashville, I lived about eight miles from my office. Every Friday, I ran to work with my dog, Oliver. One week, I had what I thought was a brilliant idea. Instead of carrying my work clothes in my backpack, I'd buy Oliver his own backpack so he could carry them.
I buckled it on and Oliver refused to move. He didn't take a single step. He just stood in the driveway looking at me as if to say, Absolutely not. So, I unpacked his backpack, stuffed everything into mine, and we headed to work the way we always had.
Looking back, I realize I made a mistake. I never stopped to ask whether the backpack was something Oliver could realistically carry. I simply decided it was his job.
Why I Don't Just Email Your Estate Planning Documents and Wish You Good Luck
If you've ever received a draft Will, Trust, Powers of Attorney, and a summary email from your attorney, you probably know the feeling. You open the attachment, see dozens of pages of legal language, and suddenly cleaning out the junk drawer, folding laundry, or taking a nap seems like a much better use of your time. I don't blame you.
Estate planning documents aren't meant to be read like a novel. Many of the most important decisions are hidden in language that can be difficult to interpret if you don't work with these documents every day.
The Best Estate Planning Metaphor I Found Was on a Hiking Trail
Every morning before I start my run, I cross the same section of trail. Then, about forty-five minutes later, I cross it again on my way back. It's become so familiar that I usually don't give it much thought. But one morning last week, I stopped, pulled out my phone, and took a picture. I remember thinking, There's got to be an estate planning metaphor here. And it turns out there was.
The Solution to Your Biggest Anxiety Might Be on a Trail with a Sausage Dog
The solution to your life's biggest anxieties might not be on a trail in the Adirondacks with a sausage dog. But you should probably check. The last time I was here was in December, the trails were covered in snow, and I was snowshoeing with one of our other dogs while trying to sort through a lot of uncertainty.
My Summer Office Has Safari Wallpaper
This summer, my office is in a familiar place: my childhood bedroom in the Adirondacks. If you see photos or videos from me over the next couple of months, you might notice the safari wallpaper in the background. I picked it out when I was eleven years old, and somehow it has survived all these years.
Every time I sit down at this desk, I'm reminded that rooms can hold stories. This one certainly does. My mom helped me choose this wallpaper. Fourteen years ago, this is also the room where she died. On paper, it sounds like this room should be filled with sadness. But that's not what I experience when I'm here.
Sometimes Love Looks Like a Bowl of Cold Water
Every morning on my run, my dog makes a stop at a house in the neighborhood where a very kind woman leaves out ice water for passing dogs. Every day, she fills a heavy bowl, places it in the shade under a tree, and freezes a huge block of ice so that the water stays cold even on hot days. It takes planning, effort and valuable freezer space.
And yet, she does it anyway.
She doesn't know which dogs will come by. But every day, she does this small thing to make life a little easier for these four-legged neighbors she'll likely never know.
It got me thinking about the ways we care for the people we love.
What My Blank Diploma Taught Me About Estate Planning
In 2005, I graduated from Dartmouth College with a degree in Russian language and literature. I worked hard and got good grades. I was the kind of student who took academics seriously.
And yet, on graduation day, I was holding a blank piece of paper.
Why?
Boots Got Adopted (And Yes, It’s Bittersweet)
Boots got adopted. She was curious, scrappy, and somehow always exactly where she shouldn’t be. The house feels quieter without her… and little less chaotic too. But mostly, it just feels different.
I got this message from Detroit Dog Rescue today about her new home:“She is fitting in incredibly well and they are obsessed with her!”
Spring has sprung at Belle Isle.
This morning it was just me, my dog, and a field of daffodils that seemed to show up overnight. We went for a run, and I kept reminding myself to take it in.
Death Readiness Doesn’t Happen in a Vacuum
My best friend came to Michigan this week, and we did what best friends do. We ran, we biked, we wandered, and we talked about everything. And somewhere in the middle of all of that, we also got her ready for her first meeting with a financial advisor.
What a Foster Puppy Taught Me about Estate Planning and Preparing the Next Person
It’s going to be bittersweet, and I’m definitely going to cry. This Saturday we’re taking our foster puppy, Boots, to an adoption event. There’s a very good chance she’ll meet the person who becomes her forever home.
We’ve spent the last month caring for little Boots. In that time, we’ve learned all of her quirks, what makes her happy, which toys she loves, what scares her, and what helps her feel safe. All this time, we’ve been preparing her for a life we won’t actually get to see. That’s the strange and beautiful part of fostering. You invest time, care, and energy into helping a dog become ready for the next chapter, and then you step aside so someone else can live that chapter with them.
Why Small Acts of Care Matter More Than You Think
In this Friday episode, Jill shares the unexpected lessons she’s learning from fostering a puppy named Boots, and how chaos, inconvenience, and small acts of care reveal what agency really looks like. Through stories about raising a guide dog puppy as a child, parenting, and estate planning, this episode reframes death readiness as something much more human: choosing small, meaningful actions even when the outcome isn’t guaranteed.
How a Poet Helped Me Face What I Feared
Sometimes a moment arrives at exactly the wrong time and exactly the right time. That’s what happened when I tried to watch Come See Me in the Good Light, the documentary about poet Andrea Gibson’s life and final years. I didn’t get far before I shut it off, not because it was too sad, but because it came too close to something I had been avoiding in my own life.
In 2020, I had surgery to remove thyroid cancer. I’m fine today, and I’m grateful. But being “fine” doesn’t mean you get to stop paying attention. Follow-up scans, biopsies, and check-ins are still part of the deal. But, for the past year, I’ve avoided all of it. I told myself I’d deal with it “soon.” Then months, and then a year, passed.
When Grief Hits Hard, Our Words Still Matter
Every once in a while, a public moment catches you off guard, not because of the celebrity involved, but because of the raw honesty you hear in their voice.
That’s what happened when I watched Jimmy Kimmel’s recent monologue honoring Cleto Escobedo II, his longtime friend and bandleader. The grief in his voice was palpable. It’s the kind that only comes from losing someone who was woven into the fabric of your life for decades.
I genuinely appreciate that Kimmel brought that vulnerability to the screen. Grief is universal, and when someone with a big platform shows what love and loss really look like, it gives the rest of us permission to feel our own.
How Hosting This Podcast Taught Me to Face Grief
You Can’t Opt Out of Grief
There’s a difference between talking about grief and living it.
My Uncle Charlie passed away at 81 after a short illness. When I first got the call, I didn’t cry. I told my husband what had happened, said I was fine, and went to bed. But the next day, when I saw photos of him on Facebook, the tears came. It was like my brain had finally caught up to my heart.
A few months ago, funeral planner Jamie Sarche joined me on the podcast to talk about why we can’t “opt out” of grief. She told me that people often try to skip the grieving process by skipping the ceremony, doing a direct cremation, keeping busy, or convincing themselves that “getting rid of the body” will make things easier. But grief doesn’t work that way. It waits for you.
When we skip the rituals that come with saying goodbye, we skip a part of healing, too.
Death Readiness Is a Family Affair
I talk about death and estate planning a lot. It’s part of my work, my mission, and my daily conversations.
But nothing brings it home quite like seeing my daughter, April, wearing our latest Death Readiness merch. This is why I do what I do.
What Seventh-Grade Frogs Taught Me About Entrepreneurship
Turns out, entrepreneurship isn’t always about a big, flashy idea. Sometimes it starts with a pile of fabric scraps and a hunch that you can make something useful (and maybe even lovable). Sometimes it grows into a podcast, a community, and a mission that feels like the work you were always meant to do.
Everyone Belongs
There’s no shortage of confusing and harmful narratives about disability in the world. Too often, families are left to sort through myths and misinformation on their own. That’s why it matters so much to keep centering truth, dignity, and respect.
Last week, I had the joy of babysitting my sweet niece while her mom (my sister-in-law) visited her son’s kindergarten class to read a story and lead an art activity about inclusion. Watching her show up for those kids reminded me that legacy takes many forms. Sometimes it looks like policy change, sometimes like advocacy, and sometimes like reading aloud in a circle of five-year-olds.
Why I Turned Off Alex Hormozi’s Podcast
Like many small business owners, I’m always working and always learning.
Podcasts are one of my favorite ways to learn. They fit into dog walks, dishwashing, and school pickup lines—moments when I want my brain to stay active even if my hands are full.
This morning, while walking my dog, I pressed play on The Game with Alex Hormozi. I’m new to his show. This was maybe my third episode.
Alex was talking about what he called “exploitation mode,” his strategy for extracting the most value from the thing you already have. I was listening in, curious about how to apply that mindset to my business.
How Our Favorite Movies Trained Us to Accept Less
When you think about “estate planning,” old rom-coms probably don’t come to mind. But maybe they should. Because for many of us, the movies we grew up watching taught us more than we realized, especially about what we’re expected to accept.
These movies quietly trained us to accept less: less agency, less credit, less space, less support. And those lessons show up everywhere, from hospital rooms to attorney meetings, from caregiving roles to family finances.
In Episode 15 of The Death Readiness Podcast, I take a closer look at these cultural scripts, and how they still shape the way many women carry the emotional and logistical weight of family life.